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以α-蒎烯为原料,在质子酸催化下发生Wagner-Meerwein重排得到α-萜品烯,再与马来酸酐发生Diels-Alder环加成反应得到α-萜品烯马来酸酐(3),然后与水合肼反应制备N-氨基-α-萜品烯马来酰亚胺(4).在冰醋酸催化下,4与各种取代苯甲醛反应,合成得到17个新型α-萜品烯马来酰亚胺基酰腙化合物5a～5q.初步探索了合成条件,并利用元素分析,1H NMR,13C NMR,LC-MS,FT-IR等多种手段对目标产物作了分析表征.初步的生物活性测试表明,大部分化合物具有一定的杀菌活性,其中4-羟基-3-甲氧基苯基-α-萜品烯马来酰亚胺基酰腙(5n)在浓度为50 mg/L时对苹果轮纹病菌、花生褐斑病菌和番茄早疫病菌的抑制率分别达91%,83.3%和76.7%.
Using α-pinene as raw material, Wagner-Meerwein rearrangement was obtained under the catalysis of proton acid to obtain α-terpinene, and Diels-Alder cycloaddition reaction with maleic anhydride gave α-terpinene maleic anhydride (3 ), And then reacted with hydrazine hydrate to prepare N-amino-α-terpinein maleimide (4). Under the catalysis of glacial acetic acid, 4 reacted with various substituted benzaldehydes to synthesize 17 novel α-terpins Ene maleimide acylhydrazone compounds 5a ~ 5q. The synthesis conditions were explored preliminarily and the target products were characterized by elemental analysis, 1H NMR, 13C NMR, LC-MS and FT-IR. The preliminary biological activity tests showed that most of the compounds had certain bactericidal activities, of which the 4-hydroxy-3-methoxyphenyl-α-terpinenyl maleimide hydrazone (5n) / L, the inhibitory rates of Alternaria alternata, Alternanthera philoxeroides and Alternaria solani were 91%, 83.3% and 76.7%, respectively.